(2-pyridyl)methylene(β-naphthyl)amine | 21756-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2-pyridyl)methylene(β-naphthyl)amine
• 英文别名: N-(2-naphthyl)-2-formimidoylpyridine；N-[((2-pyridyl)methyliden)-β-aminonaphthalene]；N-[(2-pyridyl)methyliden]-2-aminonaphthalene；β-naphthyl-(2-pyridylmethylene)amine；N-[(2-pyridyl)methylidene]-β-aminonaphthalene；N-[(2-pyridyl)methylene]-β-aminonapthalene；naphthalen-2-yl-pyridin-2-ylmethylene-amine；β-Naipy；(E)-N-(Naphthalen-2-yl)-1-(pyridin-2-yl)methanimine；N-naphthalen-2-yl-1-pyridin-2-ylmethanimine
• CAS: 21756-19-4
• 化学式: C₁₆H₁₂N₂
• 分子量: 232.285
• InChiKey: ABTDJRFFXCIENE-UHFFFAOYSA-N

物化性质

• 熔点：
  88 °C(Solv: hexane (110-54-3))
• 沸点：
  423.8±18.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-pyridyl)methylene(β-naphthyl)amine 在 盐酸 硝基苯 作用下， 以 异丙醇 、 正丁醇 为溶剂， 反应 3.0h， 生成 1-phenyl-3-(2-pyridyl)benzoquinoline
  参考文献：
  名称：

  N-（2-萘基）-2-甲酰亚胺基吡啶与取代的苯乙酮的反应

  摘要：

  DOI：

  10.1007/bf00516214
• 作为产物：
  描述：

  吡啶-2-甲醛 、 2-萘胺 以 乙醇 为溶剂， 生成 (2-pyridyl)methylene(β-naphthyl)amine
  参考文献：
  名称：

  N-[（2-吡啶基）甲基]-α（或β）-氨基萘的钌（II）-CO配合物：合成，光谱研究，晶体结构，氧化还原性质和DFT计算

  摘要：

  表征和性能的反式- （X） - [RUX 2（CO）2（α/β-NaiPy）]（1，2）（α-NaiPy（一），β-​​NaiPy（b）; X = Cl（上1），I（2））在此工作中进行了描述。通过单晶X射线衍射研究证实了该结构。这些化合物与我的反应3 NO在MeCN已分离单羰基反式- （X） - [RUX 2（CO）（乙腈）（α/β-NaiPy）]（3，4）。该配合物显示出强烈的发射性质。1和2的量子产率（ϕ  = 0.02–0.08）高于3和4（ϕ  = 0.006–0.015）。伏安图显示1和2的Ru（III）/ Ru（II）（1.3-1.5 V）电位比3和4（0.8-0.9 V）高，这可能是由于前者中两个π-酸性CO基团的配合。将复合物的电子光谱和氧化还原性质与使用极化连续谱模型（CPCM）的密度泛函理论（DFT）和时变密度泛函理论（TD-DFT）所得的结果进行了比较。

  DOI：

  10.1016/j.jorganchem.2009.09.017

文献信息

• Ruthenium(II) carbonyl complexes with N-[(2-pyridyl)methyliden]-(α/β)-aminonaphthalene: Synthesis, spectroscopic studies and DFT calculation
  作者：Shyamal Kumar Sarkar、Mahendra Sekhar Jana、Tapan Kumar Mondal、Chittaranjan Sinha

  DOI：10.1016/j.molstruc.2012.09.060

  日期：2013.3

  Reaction of RuH(Cl)(CO)(PPh 3 ) 3 with bidentate Schiffs base ligands, N-[(2-pyridyl)methyliden]-α/β-aminonaphthalene ( L 1 / L 2 ) led to the formation of photoluminescence ruthenium carbonyl complexes formulated as [RuCl(CO)(PPh 3 ) 2 (L 1 /L 2 )](PF 6 ) ( 1a / 1b ) and [RuH(CO)(PPh 3 ) 2 (L 1 /L 2 )](PF 6 ) ( 2a / 2b ) [ L 1 = N-[(2-pyridyl)methyliden]-α-aminonaphthalene and L 2 = N-[(2-pyridyl

  摘要 RuH(Cl)(CO)(PPh 3 ) 3 与双齿席夫碱配体N-[(2-吡啶基)亚甲基]-α/β-氨基萘(L 1 / L 2 )反应形成光致发光钌羰基配合物配制成 [RuCl(CO)(PPh 3 ) 2 (L 1 /L 2 )](PF 6 ) ( 1a / 1b ) 和 [RuH(CO)(PPh 3 ) 2 (L 1 /L 2 ) ](PF 6 ) ( 2a / 2b ) [ L 1 = N-[(2-吡啶基)亚甲基]-α-氨基萘和L 2 = N-[(2-吡啶基)亚甲基]-β-氨基萘]。该配合物已通过分析和光谱（IR、UV-Vis 和 1 H NMR）技术进行表征。该配合物在可见光区显示出 MLCT 带，并在室温下发射。循环伏安研究表明，Ru(II)/Ru(III) 准可逆的一个电子氧化对在 0.95-1.15 V 范围内。2a 的单晶 X 射线结构显示出围绕钌原子的扭曲八面体几何形状。DFT
• Re(I) carbonyl complexes of N-[(2-pyridyl)methyliden]-α (or β)-aminonaphthalene: Synthesis, structure, electrochemistry and DFT analysis
  作者：Ajoy Kumar Pramanik、Mahendra Sekhar Jana、Subhankar Kundu、Tapan Kumar Mondal

  DOI：10.1016/j.molstruc.2012.02.065

  日期：2012.6

  characterized by elemental analysis, spectroscopic studies, electrochemistry and X-ray crystal analysis for complex 2. Crystal structure of 2 reveals the facial geometry of the carbonyl ligand and Re is in distorted octahedral environment in the complex. The electronic structure, redox properties, absorption and emission properties have been explained based on DFT and TDDFT calculations. The complexes

  摘要 本文涉及通式 fac-[ReCl(CO)3(L1/L2)] (1/2) (L1 = N-[(2-pyridyl)亚甲基]-α-氨基萘和 L2 = N-[（2-吡啶基）亚甲基]-β-氨基萘）。配合物 fac-[ReCl(CO)3(L1/L2)] (1/2) 已被合成并通过元素分析、光谱研究、电化学和 X 射线晶体分析对配合物 2 进行表征。 2 的晶体结构揭示了羰基配体和 Re 的面部几何形状在复合物中处于扭曲的八面体环境中。基于 DFT 和 TDDFT 计算解释了电子结构、氧化还原特性、吸收和发射特性。复合物在 395-405 nm 处显示 MLCT 带，并在 310 nm 激发时在 425-435 nm 处发射，以 ILCT 转变为特征。在循环伏安研究中，当在 0.0-2.0 V 的电位范围内扫描时，复合物表现出两种不可逆的 ReII/ReI 和 ReIII/ReII 氧化反应。
• Synthesis, characterization, and cytotoxicities of platinum(II) complexes bearing pyridinecarboxaldimines containing bulky aromatic groups
  作者：Maren L. Conrad、Jennifer E. Enman、Stephen J. Scales、Haiwen Zhang、Christopher M. Vogels、Mazen T. Saleh、Andreas Decken、Stephen A. Westcott

  DOI：10.1016/j.ica.2004.07.039

  日期：2005.1

  Condensation of 2-pyridinecarboxaldehyde with several primary amines containing bulky aryl groups gave the corresponding pyridinecarboxaldimines (N-N'). Addition of these ligands to [PtCl2(coe)](2) (coe = cis-cyclooctene) gave complexes of the type cis-PtCl2(N-N') in moderate yields. The platinum complexes have been examined for their potential cytotoxicities against OV2008 (human ovarian carcinoma) and the analogous cisplatin-resistant cell line C13. (C) 2004 Elsevier B.V. All rights reserved.
• Palladium(II) complexes of N-[(2-pyridyl)methyliden]-α(or β)-aminonaphthalene: Single crystal X-ray structure of di-chloro-N-[{(2-pyridyl)methyliden}-β-aminonaphthalene]palladium(II), Pd(β-NaiPy)Cl2, spectra and DFT, TD-DFT study
  作者：P. Pratihar、S. Jha、T.K. Mondal、G. Mostafa、C. Sinha

  DOI：10.1016/j.poly.2007.05.049

  日期：2007.9

  Palladium(H) complexes of N-[(2-pyridyl)methyliden]-alpha(or beta)-aminonaphthalene (alpha or beta-NaiPy) are reported in this work. They are spectroscopically characterized along with some mixed ligand complexes, using diimine and azoimine functions. The single crystal X-ray structure of [Pd(N-(2-pyridyl)methyliden-beta-aminonaphthalene)Cl-2] has been determined. Luminescence properties of the complexes exhibit a ligand centered pi-pi* emission. Quantum yields (phi) have been calculated and it has been observed that the complexes of alpha-NaiPy show higher phi values than the complexes of beta-NaiPy. Lifetime measurements suggest bi-exponential decay and the average fluorescence lifetime varies from 1.4 to 6.8 ns. The spectroscopic properties are correlated with DFT and TD-DFT calculations in two complexes, Pd(beta-NaiPY)X-2 (X = Cl, I) and they are compared with the free ligand results. (c) 2007 Elsevier Ltd. All rights reserved.
• Zn(II)-azide complexes of diimine and azoimine functions: Synthesis, spectra and X-ray structures
  作者：D. Das、B.G. Chand、K.K. Sarker、J. Dinda、C. Sinha

  DOI：10.1016/j.poly.2006.01.033

  日期：2006.7

  Two new series of Zn(II) complexes of alpha/beta-naphthyl-(2-pyridylmethylene)amine and 1-alkyl-2-(naphthyl-alpha/beta-azo)imidazoles with N-3(-) as a counter ion are described in this article. The single crystal X-ray structure of [Zn(beta-naphthyl-(2-pyridylmethylene)amine)(N-3)(2)](2) has revealed an end-on azido bridged dimer while [Zn(1-ethyl-2-(naphthyl-beta-azo)imidazole)(2)(N-3)(2)] is a monomer. The complexes are spectroscopically characterized. Examination of luminescence properties of the complexes suggests that the Schiff bases are emissive and the naphthylazo compounds are non-emissive. (C) 2006 Elsevier Ltd. All rights reserved.